I don’t normally do this sort of thing. I have to admit, though; I’ve always found the idea of racing in women’s clothing a little compelling. I can’t explain it, but ever since I found out about it freshman year, I’ve been strangely drawn toward the High Heel Race, held on Q Street in Dupont Circle each year before Halloween. I pictured dozens of frenzied legs thundering down the street, the roar of their heels all but drowning out the cheers of the crowd – like the Running of the Bulls in Pamplona, Spain, but with drag queens. It’s danger and sex, farce and rebellion, all somehow mixed together and poured into a dress. Who am I to resist?

But there were a few hurdles I’d have to clear if I wanted to strut on Q Street with the other drag queens. First of all, I’m a slob. Ever since I got out of boarding school, I’ve worn nothing but thrift store T-shirts, torn jeans and threadbare socks. I don’t even like combing my hair. Elegance, or even some bizzaro parody of it, is way out of my league. Maybe that’s why I wanted to do this. Maybe buried deep inside me, there’s a fabulous interior decorator just dying to break free. Or maybe I was just looking for an excuse to clean myself up.

Rather than try to construct my drag queen persona alone, I decided to enlist help. I casually mentioned the project to my roommates, but they just stared, eyes wide and eyebrows twitching violently until I backed out of the room apologetically. “Awkward” doesn’t even begin to describe it. I figured most of the guys I knew would have similar reactions, so there wasn’t much point in asking them. So I wised up and asked couple of girls to make the trek out to Pentagon City with me.

Somehow, I think my shopping companions had always suspected this day would come, judging by the way they nonchalantly walked into the lady’s section at Marshall’s and started speculating over what dress size I might be. Yes, Marshall’s – I’m not what you’d call financially stable, so if I was going to buy a dress, it would have to be a cheap one. But I guess it’s all for the best, really, because the cheap dresses were the gaudiest, and I wanted to stand out from a mile away.

I took three of the cheapest, loudest dresses I could find into the dressing room, where I tried to walk quickly past the employee monitoring the area, hoping to not attract attention. No dice. The monitor stopped me and began examining my selections, looking at me like I was personally responsible for all the evils of the world. But I managed to scramble away and grab a dressing room. I don’t know how the real drag queens do it.

The first dress I tried on was a black sequined number, the sort of thing I imagine insane old ladies with 50 cats might wear to their friends’ funerals. It looked good, but I had a hell of a time getting in and out of it. While trying to take it off I ended up pinning my arm to my chest, and that point I decided this dress was just too much trouble.

I had also found a big floral muumuu, which was a lot more comfortable but made me look pregnant. The last dress was a silver crushed-velvet cocktail dress. I stared at myself in the mirror, trying to decide if it made me look fat. That’s when I knew I had found the right dress – I was already starting to think like a woman.

I stepped outside to show one of my friends, and she exclaimed, “I think you look better in a dress than I do!” This was exactly what I was hoping for. I had inspired envy. I had found my dress.

I wasn’t so lucky in the shoe department. My feet aren’t that big, but they’re larger than most women’s feet. I couldn’t find anything that would complement my dress, fit me and keep me within my budget. Looking at the piles of rejected shoes around me, I realized that no shoe store I went to would be any different. It was then that I decided to run the High Heel Race barefoot.

Perhaps that made the event a bit of a paradox – after all, how does one run a High Heel Race without heels – but I didn’t care. I wasn’t going to let a little thing like footwear hold me back. I had my dress, and with a little makeup and a tasteful headband, I would be ready for anything.

The night of the race brought cold rain whipped around by a strong wind. Walking toward the site of the race with my companions, all decked out in my dress and makeup, I was glad to be barefoot. The pavement was slick, and I chuckled to myself, imagining all the other would-be divas skidding around in their heels. My feet were a little chilly, but it was nothing I couldn’t handle. Besides, I was too caught up in the delicious reactions I was getting. People were pointing, staring, laughing and looking twice everywhere I went. Any other day of the year, I would have been wiping my nose, checking my fly and blushing uncontrollably, but for some reason, I found myself loving the negative attention. I started doing the Miss America wave and winking at passersby.

The elation was short-lived. When I got to the race I stopped short. No description I’d been given had prepared me for how obscenely huge the crowd was. You’d think the Macy’s Thanksgiving Day Parade was coming, not a herd of men in women’s clothing. Every sort of person you can imagine was there: women and men, black and white, college kids, senior citizens, some people even brought their kids. Drag queens apparently have cross-cultural appeal.

The crowd was a problem. Here I was, standing at the end of the “racetrack,” approximately four blocks from the starting line, and these people were blocking my way. I left my friends behind and began maneuvering my way through the crowd. At first I got though without too much effort, swinging my hips and winking to part the crowd whenever someone wouldn’t get out of my way. People like to keep a respectful distance from a man in a dress, and I used that to my advantage.

After about a block of this, however, even my powers of seduction and revulsion weren’t getting me through anymore, so I made a break for it, trying to run around the racetrack to the starting line. Once again, being barefoot was an asset, as I flew, surefooted, past other latecomers.

“Hey, Cinderella! You’re late for the ball!” an old woman shouted at me.

And, just like she predicted, all my barefoot hustling wasn’t enough. I turned back onto Q Street just in time to see the race begin without me.

The bulls of Pamplona have nothing on the High Heel Race. Up until now, I hadn’t been able to see any of the other “ladies.” Now, as I looked at them stampeding down the street away from me, I was dumbfounded. All this time I’d had it all wrong. I had actually been worried that my costume was too outlandish, that maybe I’d overdone it. But these people were wearing giant foam cowboy hats, Madonna-style cone bras and tinfoil tiaras. I was the most tasteful drag queen there, and suddenly I felt underdressed.

Not for long, though. As soon as the last high heel crossed the finish line, the crowd burst into the streets. Everyone, in drag and otherwise, began dancing and mingling in the streets, admiring the different outfits and taking pictures. I was photographed twice (that I was aware of, anyway) and was hit on four times in English, once in Spanish and once (I’m pretty sure) in American Sign Language. Some things just transcend language barriers.

I started talking to the other drag race divas and, for the moment at least, I felt a bond that only men wearing dresses can share with each other. For some of them, the race was an opportunity to celebrate the people they are all year. Others were first-timers like myself. But every last person I spoke to felt the same kind of pride I felt, reveling in the way the spectators stared. For that night at least, wearing a dress wasn’t just OK, it was something to be envied.